Tetrahedron

Chemo-and stereoselectivity in titanium-mediated regioselective ring-opening reaction of epoxides at the more substituted carbon

T Tanaka, K Hiramatsu, Y Kobayashi, H Ohno

Index: Tanaka, Tetsuaki; Hiramatsu, Kei; Kobayashi, Yasutaka; Ohno, Hiroaki Tetrahedron, 2005 , vol. 61, # 28 p. 6726 - 6742

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Citation Number: 16

Abstract

Chemo-and stereoselectivity in the ring-opening reaction of epoxides with a reagent prepared from allylmagnesium halide and chlorotitanium triphenoxide is described. It has been proven that the allylating reagent can also be used for the reaction of epoxides bearing a tert-butyl ester, amide, or acetal moiety, and that the epoxide cleavage regioselectively takes place at the more substituted carbon in all cases. Interestingly, while the reaction of ...